We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Kailua

Check availability
Refine search

Search within

 

Desired stay

 

Price range

 
$500$56,000
 

Bedrooms

Studio10+
 

Bathrooms

14+
 

Sleeps

110+
 

Traveler rating

1.05.0
 

Property type

 

Amenities

 

Suitability

 
Own a rental property?
Want more exposure for your rental? Get listed in TripAdvisor Vacation Rentals (in partnership with FlipKey).
Vacation Rental Calculator
Compare & Save »
Free Newsletter

Sign up to hear about gorgeous vacation rentals, the latest deals, exciting destinations, and more.

Rental properties provided by
Learn more
Don't see the property you rented? Tell us more about it »

Vacation Rentals in Kailua, Oahu

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.

 
more     
Tip: Refine your search by price, amenities, & more (see left column).
Searching … 0% complete
161 Trusted Kailua Rentals
List View
loading...
Also consider
$125 / night
1 Bedroom, sleeps 2
1 Bathroom
$125 - $845 / night
5 Bedrooms, sleeps 10
5 Bathrooms
$75 - $265 / night
5 Bedrooms, sleeps 22
5 Bathrooms
$175 - $225 / night
1 Bedroom, sleeps 4
1 Bathroom
$900 / night
8 Bedrooms, sleeps 16
5 Bathrooms

Traveler Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 3 Bedrooms, sleeps 9
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$295
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$385
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 3 Bedrooms, sleeps 7
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$529
Minimum rental - 2 nights
Check availability
Map unavailable
Also consider
$125 / night
1 Bedroom, sleeps 2
1 Bathroom
$125 - $845 / night
5 Bedrooms, sleeps 10
5 Bathrooms
$75 - $265 / night
5 Bedrooms, sleeps 22
5 Bathrooms
$175 - $225 / night
1 Bedroom, sleeps 4
1 Bathroom
$900 / night
8 Bedrooms, sleeps 16
5 Bathrooms
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$585
Minimum rental - 2 nights
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 4
  • 1 Bathroom
  • Professional
EMAIL MANAGER
Night:
$395 - $425
Minimum rental - 1 week
Check availability
  • Rental Home
  • 3 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
$695 - $795
Week:
$4,795 - $5,495
Month:
$15,000 - $18,000
Minimum rental - 5 nights
Check availability
  • Rental Home
  • 5 Bedrooms, sleeps 8
  • 7 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
$1,500
Week:
$8,500
Minimum rental - 4 weeks, 2 nights
Check availability
Hawaii, Oahu, Kailua Vacation Rentals
  • Condo/Apartment
  • 1 Bedroom, sleeps 2
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$85 - $140
Week:
$595 - $980
Month:
$2,550 - $2,700
Minimum rental - 3 nights
Check availability
Hawaii, Oahu, Kailua Vacation Rentals
  • Villa
  • 10 Bedrooms, sleeps 18
  • 11 Bathrooms
  • Professional
EMAIL MANAGER
Week:
$35,000 - $52,500
Minimum rental - 1 week
Check availability
Map unavailable
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 7
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$695 - $775
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$450 - $700
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$690 - $850
Week:
$4,830 - $5,950
Month:
$15,000 - $18,000
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$750 - $850
Month:
$19,125
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$495 - $775
Minimum rental - 2 nights
Check availability
Map unavailable
  • Rental Home
  • 1 Bedroom, sleeps 2
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
$185
Minimum rental - 3 nights
Check availability
Hawaii, Oahu, Kailua Vacation Rentals
  • Rental Home
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$585
Minimum rental - 2 nights
Check availability
Map unavailable

Kailua Vacation Rental Advice

Posted by KailuaMama, Jan 13, 2012
... are unaware of the illegal vacation rental situation here and really can't be held responsible. Others simply don't care. Not going to bother posting links but if you're interested in reading more about it you can google "oahu illegal vacation rentals." The controversy has been going on ... more
Posted by LUFCkev, Jan 5, 2012
... that the vast majority of vacation rentals in this area are illegal. Also, despite the competition being 100% legitimate, there's a free online entry route, but also a method of entry where you get extra entries through a premium rate text/phone call. I'd hate to enter, win ... more
Posted by msfuzz, Jan 6, 2012
epi, this year Obama did rent a legally permitted vacation rental in Kailua!! ... more
Posted by amberloo, Jan 6, 2012
... the owner requires one-month vacation rentals, plays the "Obama" game, or just doesn't rent it out more than once a month or twelve times a year, the County really can't touch them. However, there has long been talk of closing this loophole. They couldn't just change ... more
Posted by KailuaMama, Aug 13, 2011
According to this the address for Savannah's Cabana is 156-A Ainoni Street. http://www.yelp.com/biz/savannahs-cabana-kailua And no, it's not on the list of legally permitted vacation rentals. http://honoluludpp.org/HotIssues/NUCreport.pdf ... more
Posted by swmarket, Jun 24, 2011
... all the details and permits. She's certainly not a legal rental if that matter to you. I'd be concerned since one of her sites says that "we can only rent it for a week each month"............smells like they've already had trouble with neighbors about vacation rental ... more
Posted by amberloo, Jun 24, 2011
... get around the laws against vacation rentals on ... ... a home out as a vacation rental up to 12 times each year without breaking any laws; whether for a day, week or month at a time. In theory, a place can't be rented out more than once during each 30 ... more
Posted by swmarket, Jun 24, 2011
... not a permitted or licensed vacation rental instead, and that they are using a loophole to work around the lack of a permit. But my goal here was really to try and show Boxer that research is easy and a good thing. I don't know that this property is ... more
Posted by ubudfitnessbali, Jul 12, 2011
... really like Trinity Properties for vacation rentals. They have access to almost all the rentals on Oahu. Their website is www.trinityproperties.com. The reason why I like to use them is that you can talk to them on the phone and they can help you identify the best properties ... more
Posted by dusty56438, Nov 25, 2010
... are a distance from the pond and may not be visible from the waterfront mentioned. Contact them for an address. Then you can easily find it. By the way, you can get a lot of Kailua info from the main site of Kailua Vacation Rentals above. Dining, beaches, attractions, etc ... more
See all sites
Cruise Critic

The ultimate cruise resource: cruise reviews, deals, news and advice.

SeatGuru

The world's most comprehensive source for airline seats, airline info, & in-flight amenities.

Family Vacation Critic

The best family vacations start here.